149776-82-9

Upstream product

• 174788-39-7 4-(tert-butyldimethylsilyloxy)methyl-3,3-dimethylcyclohexanone 
• 487-51-4 4-carbethoxy-3-methyl-2-cyclohexen-1-one 
• 174788-20-6 2-cyanomethyl-1,3,3-trimethyl-4-hydroxymethylcyclohex-1-ene 
• 174788-15-9 4-(tert-Butyl-dimethyl-silanyloxymethyl)-2-dimethoxymethyl-1,3,3-trimethyl-cyclohexanol 
• 174788-16-0 4-(tert-butyldimethylsilyloxy)methyl-3,3-dimethyl-1-trimethylsilyloxycyclohex-1-ene 
• 150665-29-5 4-(tert-butyldimethylsilyloxy)methyl-3,3-dimethyl-2-formyl(dimethylacetal)cyclohexanone 
• 174788-19-3 2-cyanomethyl-1,3,3-trimethyl-4-(tert-butyldimethylsilyloxy)methylcyclohex-1-ene 
• 150665-30-8 1-methoxy-2-formyl(dimethylacetal)-1,3,3-trimethyl-4-(tert-butyldimethylsilyloxy)methylcyclohexane 
• 174788-18-2 5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,6,6-trimethyl-cyclohex-1-enecarbaldehyde 
• 171504-24-8 [5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,6,6-trimethyl-cyclohex-1-enyl]-methanol 
• 174788-43-3 2-bromomethyl-1,3,3-trimethyl-4-(tert-butyldimethylsilyloxy)methylcyclohex-1-ene 
• 117106-83-9 4-(tert-Butyl-dimethyl-silanyloxymethyl)-3-methyl-cyclohex-2-enone 
• 58403-93-3 4-hydroxymethyl-3-methyl-2-cyclohexen-1-one 
• 174788-38-6 4-hydroxymethyl-3-methyl-2-cyclohexene-1-ol 

Relevant academic research and scientific papers

A cycloaddition approach to tricyclic taxoid skeletons

A cycloaddition approach to the functionalized tricyclo[9.3.1.03,8]pentadecene skeleton contained in Taxol is described. The cyclohexenone 13 was converted as illustrated to the nitrile-aldehyde 24 to which the diene and acetylenic side chains were attached by sequential nucleophilic additions. Removal of the trimethylsilyl protecting group and Dess-Martin oxidation afforded the triene 35. Microwave-assisted thermal cyclization stereoselectively generated the tricyclic ketone 36 whose structure was further established by conversion to the aromatic system 37 upon treatment with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ). An epoxidation sequence was developed to introduce the epimeric C13 alcohol 47 as required for this cycloaddition strategy. Alternatively, an allylic oxidation (CrO3, 3,5-dimethylpyrazole) afforded the C13 ketone 49.

An Intramolecular Diels-Alder Approach to Tricyclic Taxoid Skeletons

A direct, intramolecular cycloaddition route to functionalized tricyclic taxanes is described.This will facilitate the preparation of potentially useful analogues and ultimately the total synthesis of taxol.The cyclohexenone 2 is converted as illustrated to the trimethylcyclohexene 9 to which the diene and acetylenic side chains are attached by sequential nucleophilic additions.Removal of the trimethylsilyl protecting group and Dess-Martin oxidation afforded the triene 13.Microwave assisted thermal cyclization generated the tricyclic ketone 14 stereoselectively whose structure was further established by conversion to the aromatic system 15 upon treatment with DDQ.